Di-tert-butylzinc

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Di-tert-butylzinc
Di-tert-butylzinc.png
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Names
IUPAC name
Bis(dimethylethyl)zinc
Other names
Di-tert-butylzinc
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/2C4H9.Zn/c2*1-4(2)3;/h2*1-3H3; X mark.svgN
    Key: KYHHMFUFEIHUHB-UHFFFAOYSA-N X mark.svgN
  • InChI=1/2C4H9.Zn/c2*1-4(2)3;/h2*1-3H3;/rC8H18Zn/c1-7(2,3)9-8(4,5)6/h1-6H3
    Key: KYHHMFUFEIHUHB-UUODNYSZAB
  • CC(C)(C)[Zn]C(C)(C)C
Properties
C8H18Zn
Molar mass 179.61 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Di-tert-butylzinc is a compound with the formula ZnC8H18. This compound is used as a meta activating reagent in the syntheses of N,N-dimethyl-3-iodoaniline from N,N-dimethylaniline. [1]

Synthesis

Di-tert-butylzinc is obtained from the reaction between tert-butyllithium and zinc chloride. [2]

2 (CH3)3CLi + ZnCl2 → Zn(C(CH3)3)2 + 2 LiCl

References

  1. ↑ Armstrong, David R.; Clegg, William; Dale, Sophie H.; Hevia, Eva; Hogg, Lorna M.; Honeyman, Gordon W.; Mulvey, Robert E. (2006). "Directedmeta-Metalation Using Alkali-Metal-Mediated Zincation". Angewandte Chemie International Edition. 45 (23): 3775–8. doi: 10.1002/anie.200600720 . PMID   16671139.
  2. ↑ Mulvey, Robert E.; Garden, Jennifer A. (2014), "Di-tert-butylzinc", Encyclopedia of Reagents for Organic Synthesis , Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289x.rn01774, ISBN   978-0-470-84289-8


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